CHEM 760/7600 - Advanced Carbohydrate Chemistry
Semester: Fall 2018Professor: F.I. Auzanneau | Discipline: Organic | Campus: Guelph
Chemistry CHEM*7600 is a one-semester course in covering the chemistry and biological chemistry of carbohydrates. This course will apply concepts learned in Chem*2700 and Chem*3750 to carbohydrate molecules and cannot be taken if the student has already taken Chem*4740 with Prof Auzanneau in a previous offering.
Specific Learning Objectives:
- To learn about the structural fundamentals of carbohydrates.
- To learn the basic biological importance of oligo-and polysaccharides.
- To learn fundamentals concepts of synthetic carbohydrate chemistry and to be able to design syntheses of organic molecules of moderate complexity.
- To learn then be able to use one dimension and two dimension NMR experiments to characterize synthetic molecules.
- To be able to survey the literature and identify a question that has yet to be answered in the area of glycobiology.
- To design a sound research proposal that would allow answering the question identified
- To learn the basic skills required to write a Grant proposal in the NSERC format.
- To concisely present the proposed research orally to a mixed audience.
There is no “official” text-book for this course. However the lecture content will be based on the following texts as well as literature examples:
- Title: Organic synthesis with carbohydrates
Author: Boons, Geert-Jan. Hale, Karl.
Publisher: Malden, MA: Blackwell Science, 2000.
- Title: Essentials of carbohydrate chemistry and biochemistry
Author: Lindhorst, Thisbe K.
Publisher: Weinheim : Wiley-VCH, c2003.
Additional resources are:
Title: Preparative carbohydrate chemistry
Author: Hanessian, Stephen.
Publisher: New York : Marcel Dekker, c1997.
Title: Modern Methods in Carbohydrate Synthesis
Authors: Shaheer H. Khan, Roger A. O’Neill
Publisher: Harwood Academic publishers
Title: Carbohydrates in chemistry and biology
Authors: Ernst, Beat Hart, Gerald W, Sinaÿ, Pierre
Publisher: Weinheim ; New York : Wiley-VCH, c2000.
Other resources such as pdf files of literature articles as well as lecture material will be available for download from the course web-page throughout the semester.
Grades will be calculated as follow:
Research proposal: 15%
NMR practice: 5%
NMR practice: This will be based on “real” set of NMR data.
Presentation and Research Proposal:
Each student will search the glycobiology literature and design an original research project. Such project could be aimed towards the synthesis of molecules relevant to glycobiology, method development for synthetic carbohydrate chemistry etc… You will write up this research proposal in an NSERC format, including Background/Relevance, descriptive short term goals, long term goals and impact. You will also be asked to provide an appropriate budget. We will have one extra meeting to discuss grant proposal writing.
Each student will present his/her proposal in class (10 min), outlining the topic of the study, and the method proposed (with details). The presentation will be followed by a 2 min discussion in class. Graduate students will present towards the last scheduled class times
Midterm; The midterm examination will take place on Saturday October 27, 10-11:30, location TBD
Final: The final examination TBD
- Structure of monosaccharides: configurations, ring size, conformations, mutarotation, anomeric effect
- Biological relevance of carbohydrates: disaccharides, oligosaccharides, polysaccharides, biosynthesis and synthetic biochemical tools
- Carbohydrate Synthetic Chemistry: A. Protecting groups in carbohydrate chemistry and synthetic strategies: Alkyls, acyls, silyls, acetals and ketals, selectivity etc… The daunting task of multi-step carbohydrate synthesis! B.The glycosylation reaction: when titans collide, the challenge of carbohydrate chemistry. Principle of glycosylation, armed-disarmed glycosyl donors, participating groups, anomeric effect and kinetic anomeric effect, glycosylation methods: Fisher, Koenigs-Knorr, Helfrich, thioglycosides, trichloroacetimidates and many others…
- NMR of carbohydrates: chemical shifts, coupling constants, 1D, 2D (real life examples)
- Mon: 8:30 am - 9:20 am in MacN 101/EIT 2053
- Wed: 8:30 am - 9:20 am in MacN 101/EIT 2053
- Fri: 8:30 am - 9:20 am in MacN 101/EIT 2053